In my last post I discussed how to make a mediocre extracurricular essay better (in about 30 minutes). Time to talk about what makes an essay amazing.

You’ll recall from the Ira Glass on Storytelling YouTube videos that what makes a story great is a great narrative followed by a great insight.

Here are some of the qualities of an amazing essay:

The story is unusual in either content, structure or both.

A “wow” moment.

The ending is both surprising and inevitable.

The ending makes the reader do a little bit of work.

I find it’s best to illustrate by example, so here are the premises for two amazing essays:

Premise of the “Dead Bird” essay: a girl is doing her homework one day when her cat claws a bird (almost) to death and as the narrator tries desperately to save the bird’s life she makes a life-changing realization about a friend of hers who was killed.

Premise of the “I Shot My Brother” essay: a boy has a chance to save his brother’s life, but in order to do so he’ll have to shoot him.

Are you interested? Good.

Note that I haven’t given away the ending yet. I want you to read both of them first so you can experience them as pieces of writing before we analyze what makes each one amazing.

The moment when she realizes that her struggle to let the bird go parallels her struggle to let her friend go. It’s not explicit, so you have to look for it. But it’s there.

3. The ending is both surprising and inevitable

Why surprising? We didn’t expect her to make peace with the bird’s death, or her friend’s.

Why inevitable? Now that I think about it, of course she’d have to accept the bird’s death, and her friend’s.

4. The ending makes the reader do a little bit of work.

Look at that ending again--what does it mean?

The wind, the sky, the dampness of the soil on my hands whispered to me, “The bird is dead. Kari has passed. But you are alive.” My breath, my heartbeat, my sweat sighed back, “I am alive. I am alive. I am alive.”

It’s not explicit. I would call this a “poetic” ending, and I’ll define “poetic” in this way: it leaves something unaccounted for. To get the meaning you have to think about it a bit, and different people may have different interpretations. Note that it’s easy to do this poorly and hard to do this well. In terms of what the ending to this essay means, I won’t ruin it by trying to explain it. I’ll let you decide for yourself. (And that’s not a tease, by the way, that’s a gift.)

The I Shot My Brother essay: why I think it’s amazing

1. a. Unusual content: what kind of person shoots his brother? And what kind of person shoots his brother to save his brother's life? Not many people.

b. Unusual structure: non-chronological order of events (starts with the end). Cinematic time-jumps.

c. Unusual style: great dialogue. Realistic characters. Memorable visual details. One of the best openings I have ever read.

2. The “wow” moment: the moment he has to shoot his brother in order to save his life.

Double wow: he’s also been looking to get back at his brother, so shooting him is both an “I love you” and “I hate you” moment.

Triple wow: the moment of violence ends up being the catalyst for ultimately bringing them together...

3. The ending is both surprising and inevitable

Surprising: no way will these two reconcile.

Inevitable: of course they’ll reconcile.

Also surprising: even if I suspected they would reconcile, I didn’t expect it would happen in this way.

4. The ending makes the reader do a little bit of work.

Again, look at that ending--what does it mean?

Smiling, I open Jon’s Jansport backpack and neatly place this essay inside and a chocolate taffy with a note attached.

Twenty minutes have passed when the door abruptly opens.

“Guess what the doctor just said?” my brother cries, unable to hide his exhilaration. I look up and I smile too.

Again, I won’t spell it out. Just think about where his relationship with his brother started and think about where it is now.

Also--and I just noticed this--both of these essays end with some kind of redemption. I’m not saying that’s required for an amazing essay, but I think it’s part of makes my heart swell every time I read these two.

Keep in mind that these are not the only qualities of an amazing essay or even required to make your essay amazing, these are simply qualities that I have observed in essays that I find amazing.